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...and that script is running which sends me an e-mail saying there was an issue.

Like a lot of things late in the game of developing my website, it is hard to troubleshoot if you don't have my entire code base, and yet I am hoping someone out there has seen something similar and may have som ideas of how to fix this?!

It would be a real bummer if I - as the Admin - get an e-mail every time someone backs up from a PM to their Inbox!!!!!

That will ultimately come down to your rewrite rules. If I had to guess, one of them has a trailing / on it, and the rewrite engine either only handles it with the trailing front slash or doesn't handle it. One or the other would trigger an error since it is now looking for a directory which presumably doesn't exist.

That will ultimately come down to your rewrite rules. If I had to guess, one of them has a trailing / on it, and the rewrite engine either only handles it with the trailing front slash or doesn't handle it. One or the other would trigger an error since it is now looking for a directory which presumably doesn't exist.

Your rewrite can just take /? on it to make it optional.
The source image paths are irrelevant. Unless its somehow matching your rewrite rules which is very easy to do. Your current rules only check to see if a file matches, otherwise it goes ahead and rewrites. Assuming the style is overall the same, not matching a filepath for an image would attempt to rewrite it. I wouldn't think that would cause a 404 on a page though; all that should do is show a broken image link since the image itself is a 404.